TW202022047A - Heat-curable resin composition, heat-curable resin film and semiconductor device - Google Patents

Abstract

Provided is a heat-curable resin composition exhibiting a superior handling property and workability in the form of a film, having a high adhesion to a base material, and capable of yielding a cured product with a low elasticity. The heat-curable resin composition contains: (A) 90 to 10 parts by mass of a silicone-modified epoxy resin; (B) 10 to 90 parts by mass of a maleimide compound having a weight-average molecular weight (Mw) of 2,500 to 50,000; and (C) a curing catalyst, provided that a total of the components (A) and (B) is 100 parts by mass.

Description

Thermosetting resin composition, thermosetting resin film and semiconductor device

The present invention relates to a thermosetting resin composition, a thermosetting resin film containing the thermosetting resin composition, and a semiconductor device using the thermosetting resin film.

In recent years, electronic devices such as mobile phones, smart phones, ultra-thin liquid crystal and plasma TVs, and lightweight notebook computers have been miniaturized. Therefore, electronic components used in these electronic devices are moving toward high-density integration and further high-density packaging. As a manufacturing method of the electronic component, the mainstream is a method of packaging semiconductor elements mounted on a large substrate or 12-inch wafer by one-shot molding. As an encapsulating resin for a large area, a film material or sheet is used from the viewpoint of handleability and moldability.

As one of the resins used for the film material, phenoxy resin (Patent Document 1) can be cited. Although the resin composition using the phenoxy resin is excellent in moldability and handleability, on the other hand, there is also a problem of increased warpage when packaging large substrates and 12-inch wafers.

In addition, as a resin or a resin composition used for a film material, a resin composition containing a polyimide resin as a main component is described in Patent Document 2; it is described in Patent Document 3; and a maleimide compound is contained , Epoxy compound and anionic catalyst composition.

However, polyimide resins generally have the property of being only soluble in high-boiling solvents, so the solvent may not be sufficiently removed during the film preparation process. As a result, problems such as generation of voids and peeling from the substrate may occur during molding. In addition, the high-molecular maleimide compound has poor compatibility with epoxy resins, and separates during curing, resulting in problems such as decreased adhesiveness or decreased mechanical strength. Existing technical literature Patent Literature

Patent Document 1: Japanese Patent Application Publication No. 2017-039305 Patent Document 2: Japanese Patent Application Publication No. 2017-145289 Patent Document 3: International Publication No. W2017/027482

The problem to be solved by the invention

Therefore, the object of the present invention is to provide a thermosetting resin composition. It has excellent handleability and operability when used as a film, and has high adhesion to the substrate, and its cured product has low elasticity. way of solving the problem

In order to solve the above-mentioned problems, the inventors have conducted intensive studies and found that the following thermosetting resin composition can achieve the above-mentioned objects, thus completing the present invention. That is, this invention is an invention which provides the following thermosetting resin composition.

[1] A thermosetting resin composition comprising the following components (A) to (C), (A) Silicone modified epoxy resin: 90-10 parts by mass; (B) Maleimide compound having a weight average molecular weight (Mw) of 2500 to 50000: 10 to 90 parts by mass; and (C) curing catalyst, However, the total of (A) component and (B) component is 100 mass parts.

[2] The thermosetting resin composition according to [1], further comprising (A') an epoxy resin other than (A) the silicone-modified epoxy resin.

在通式(8)與通式(9)中，X彼此獨立地表示氫原子、非取代或取代的碳原子數1~6的一價烴基、烷氧基或烷氧基烷基，R³ 表示非取代或取代的不具有脂肪族不飽和基團的一價烴基，R⁴ 表示縮水甘油基，R⁵ 表示任選具有氧原子的非取代或取代的二價烴基，R⁶ 彼此獨立地表示氫原子、甲基或三氟甲基，k為8以上的整數，p為0以上的整數。[3] The thermosetting resin composition according to [1] or [2], wherein (A) the silicone-modified epoxy resin is at least one type of silicon represented by the following general formula (8) or (9) Ketone modified epoxy resin,

In the general formula (8) and general formula (9), X independently represents a hydrogen atom, an unsubstituted or substituted monovalent hydrocarbon group with 1 to 6 carbon atoms, an alkoxy group or an alkoxyalkyl group, R ³ Represents an unsubstituted or substituted monovalent hydrocarbon group without an aliphatic unsaturated group, R ⁴ represents a glycidyl group, R ⁵ represents an unsubstituted or substituted divalent hydrocarbon group optionally having an oxygen atom, and R ⁶ represents independently of each other A hydrogen atom, a methyl group, or a trifluoromethyl group, k is an integer of 8 or more, and p is an integer of 0 or more.

在通式(1)中，n為1~50的整數，R¹ 獨立地表示選自碳原子數1~40的直鏈或支鏈的亞烴基、任選具有雜原子的碳原子數為3~20的二價環狀烴基、-O-、-NH-、-S-以及-SO₂ -中的一種或二種以上二價基團。[4] The thermosetting resin composition according to any one of [1] to [3], wherein (B) the maleimide compound is a bismaleimide compound represented by the following formula (1) ,

In the general formula (1), n is an integer from 1 to 50, and R ¹ independently represents a linear or branched alkylene group selected from 1 to 40 carbon atoms, and the number of carbon atoms optionally having heteroatoms is 3. ~20 divalent cyclic hydrocarbon group, one or two or more divalent groups among -O-, -NH-, -S- and -SO ₂ -.

在通式(2)中，A獨立地表示含有芳香族環或脂肪族環的四價有機基團，B為具有任選含有雜原子的二價脂肪族環的碳原子數為6~18的伸烷基鏈，Q獨立地表示碳原子數6以上的直鏈伸烷基，R獨立地表示碳原子數6以上的直鏈或支鏈的烷基，n’表示1~10的整數，m表示0~10的整數。[5] The thermosetting resin composition according to any one of [1] to [3], wherein (B) the maleimide compound is a compound represented by the following general formula (2),

In the general formula (2), A independently represents a tetravalent organic group containing an aromatic ring or an aliphatic ring, and B is a divalent aliphatic ring optionally containing heteroatoms with 6 to 18 carbon atoms Alkylene chain, Q independently represents a straight chain alkylene with 6 or more carbon atoms, R independently represents a straight or branched chain alkyl with 6 or more carbon atoms, n'represents an integer from 1 to 10, m Represents an integer from 0 to 10.

需要說明的是，上述結構式中的未鍵合有取代基的鍵為與在通式(2)中形成環狀醯亞胺結構的羰基碳鍵合的鍵。[6] The thermosetting resin composition according to [5], wherein A in the general formula (2) is represented by any one of the following structures,

It should be noted that the bond to which the substituent is not bonded in the above structural formula is a bond to the carbonyl carbon forming the cyclic amide structure in the general formula (2).

[7] The thermosetting resin composition according to any one of [1] to [6], wherein the (C) curing catalyst is a curing agent selected from (C1) epoxy resins, (C2) curing accelerators And (C3) at least one of a polymerization initiator.

[8] The thermosetting resin composition according to any one of [1] to [7], wherein the (C) curing catalyst is an imidazole compound.

[9] A thermosetting resin film comprising the thermosetting resin composition described in [1] to [8].

[10] A semiconductor device packaged with the thermosetting resin film described in [9]. Effect of invention

The thermosetting resin composition of the present invention can obtain a cured product that is excellent in handleability and handleability during film formation, has excellent adhesion to a substrate, and has low elasticity. In addition, when the thermosetting resin composition of the present invention is formed into a film, even if the film is used to encapsulate a large substrate or a 12-inch wafer, the warpage is small, and there is no void or peeling from the substrate during molding. , Excellent adhesion to the substrate.

detailed description

Hereinafter, the present invention will be explained in more detail. (A) Silicone modified epoxy resin

The silicone-modified epoxy resin of component (A) can be composed of, for example, an epoxy resin containing an alkenyl group, and the following average composition formula (3), and the number of silicon atoms in one molecule is 10 to 100 The organohydrogen polysiloxane is prepared by the hydrosilylation reaction.

H _a R ³ _b SiO _{(4-ab) / 2} (3) The average composition of the organohydrogen polysiloxane represented by the formula (3), the number of silicon atoms in one molecule is preferably 20 to 80, and one molecule is The number of hydrogen atoms (SiH groups) bonded to the silicon atom is preferably 1 to 5, more preferably 2 to 4, particularly preferably 2.

In the above average composition formula (3), a is a number ranging from 0.005 to 0.1, preferably 0.01 to 0.05, b is a number ranging from 1.8 to 2.2, preferably 1.9 to 2.0, and the sum of a+b is 1.81 to 2.3 , Preferably a number from 1.91 to 2.05.

In the above average composition formula (3), R ^{3 is an} unsubstituted or substituted monovalent hydrocarbon group having no aliphatic unsaturated group, and the number of carbon atoms is 1-10, particularly preferably 1-8. Examples include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, hexyl, cyclohexyl, octyl, and decyl; phenyl, xylyl, toluene Aryl groups such as benzyl groups, phenethyl groups, and phenylpropyl groups; and chloromethyl, bromoethyl, and trifluoromethyl groups in which part or all of the hydrogen atoms of their hydrocarbon groups are replaced by halogen atoms such as chlorine, fluorine, and bromine. Halogen-substituted monovalent hydrocarbon groups such as fluoropropyl and the like.

As an epoxy resin containing an alkenyl group, the general formula shown below can be mentioned, for example.

In the above general formulas (4) to (7), R ⁴ is a glycidyl group. X is independently a hydrogen atom, an unsubstituted or substituted monovalent hydrocarbon group having 1 to 6 carbon atoms, an alkoxy group, or an alkoxyalkyl group. R ^{6 is} independently a hydrogen atom, a methyl group, or a trifluoromethyl group. n is an integer of 0 or more, preferably 0 or an integer of 1-50, more preferably 0 or an integer of 1-10. m is an integer of 0 or more, preferably 0 or an integer of 1 to 5, more preferably 0 or 1.

Examples of the unsubstituted or substituted monovalent hydrocarbon group having 1 to 6 carbon atoms represented by X in the above general formulae (4) to (7) include, for example, methyl, ethyl, propyl, and butyl Alkyl groups such as vinyl, allyl and isopropenyl groups; aryl groups such as phenyl group. The unsubstituted or substituted alkoxy group represented by X in the above general formulas (4) to (7) includes methoxy, ethoxy, propoxy and the like. Examples of unsubstituted or substituted alkoxyalkyl groups include ethoxyethyl and ethoxymethyl. Among them, X is preferably a hydrogen atom and a methyl group. X in the above general formula may be the same or different.

The hydrosilylation reaction between the alkenyl group-containing epoxy resin and the organohydrogenpolysiloxane represented by the general formula (3) can be carried out under known reaction conditions. For example, the reaction can be carried out using a platinum-based catalyst.

As the silicone-modified epoxy resin obtained by such a hydrosilylation reaction, a silicone-modified epoxy resin represented by the following general formula is particularly preferred.

In the above general formula (8) and general formula (9), X, R ³ , R ⁴ and R ⁶ have the same meanings as above. R ⁵ represents an unsubstituted or substituted divalent hydrocarbon group optionally having an oxygen atom. K is an integer of 8 or more, preferably 18 to 78, and more preferably 28 to 68, and p is 0 or more, preferably 1 to 50, more preferably an integer of 1 to 10.

R ^{5 is} preferably an alkylene group optionally having an oxygen atom or a hydroxyl group and the like, and examples thereof include the following groups. -CH ₂ CH ₂ CH ₂ --CH ₂ CH ₂ CH ₂ -O- -O-CH ₂ -CH(OH)-CH ₂ -O-CH ₂ CH ₂ CH ₂ --O-CH ₂ -CH(OH ) -CH ₂ -O-CH ₂ CH ₂ CH ₂ -O- -O-CH ₂ CH ₂ CH ₂ --O-CH ₂ CH ₂ CH ₂ -O- It should be noted that in the second part of R ⁵ Among the groups exemplified by the valence hydrocarbon group, the bond at the left end is a bond to the benzene ring having the group X of the general formula (8) or the benzene ring having the group OR ⁴ of the general formula (9). The bond at the right end is a bond to the silicon atom of Si (R ³ ) in general formula (8) and general formula (9). The silicone-modified epoxy resin may be used alone or in combination of two or more.

(A’) Epoxy resins other than (A) silicone modified epoxy resin Examples of epoxy resins other than silicone modified epoxy resins include bisphenol A type epoxy resins, bisphenol F type epoxy resins, bisphenol S type epoxy resins, novolac type epoxy resins, Cresol novolac type epoxy resin, bisphenol A varnish type epoxy resin, bisphenol F varnish type epoxy resin, stilbene type epoxy resin, epoxy resin containing triazine skeleton, epoxy resin containing fluorene skeleton, Triphenol alkane epoxy resin, biphenyl epoxy resin, xylene epoxy resin, biphenyl aralkyl epoxy resin, naphthalene epoxy resin, dicyclopentadiene epoxy resin, grease Cyclic epoxy resins, aminophenol epoxy resins, hydrogenated bisphenol epoxy resins, alcohol ether epoxy resins, polyfunctional phenols, anthracene and other polycyclic aromatic diglycidyl ether compounds, as well as Phosphorus compounds are introduced into these epoxy resins containing phosphorus. Among them, from the viewpoint of operability, it is preferably a liquid bisphenol A type epoxy resin, a liquid bisphenol F type epoxy resin, a liquid naphthalene type epoxy resin, and a liquid amino group that are liquid at room temperature. Phenolic epoxy resin, liquid hydrogenated biphenyl epoxy resin, liquid alcohol ether epoxy resin, liquid cycloaliphatic epoxy resin, liquid fluorene epoxy resin. These epoxy resins other than the silicone-modified epoxy resin may be used alone or in combination of two or more kinds.

(A) The compounding amount of the silicone-modified epoxy resin is sufficient as long as it is an effective amount that imparts low elasticity, flexibility, and impact resistance to the cured product. Compared with (A) the silicone-modified epoxy resin and ( A') The total amount of epoxy resins other than silicone-modified epoxy resin, (A) The compounding amount of silicone-modified epoxy resin is 5-100% by mass, preferably 10-80% by mass, particularly preferred It is 20~70% by mass. If the compounding amount of the silicone-modified epoxy resin is too small, the cured product may lack flexibility and deteriorate thermal shock resistance; if the compounding amount is too large, the composition may increase in viscosity, which may result in poor workability.

In the composition of the present invention, the content of (A) silicone-modified epoxy resin is preferably 10 to 90 parts by mass relative to 100 parts by mass of the total of the component (A) and the component (B) described later. It is more preferably 20 to 60 parts by mass, and still more preferably 20 to 50 parts by mass.

(B) Maleimide compound In the present invention, as the (B) maleimide compound, a maleimide compound having a weight average molecular weight (Mw) of 2500 to 50,000, preferably 3,000 to 30,000 is used. In the case where the weight average molecular weight is less than 2500, there is a possibility that workability is poor when a film is formed using the composition of the present invention. On the other hand, if the weight average molecular weight exceeds 50,000, its compatibility with epoxy resins is greatly reduced. It should be noted that the weight average molecular weight refers to the weight average molecular weight measured by gel permeation chromatography (GPC) under the following conditions.

[GPC measurement conditions] Developing solvent: tetrahydrofuran Flow rate: 0.6mL/min Column: TSK Guardcolumn SuperH-L TSKgel SuperH4000(6.0mmI.D.×15cm×1) TSKgel SuperH3000(6.0mmI.D.×15cm×1) TSKgel SuperH2000(6.0mmI.D.×15cm×2) (All manufactured by Tosoh Corporation) Column temperature: 40℃ Sample injection volume: 20μL (sample concentration: 0.5% by mass-tetrahydrofuran solution) Detector: Differential Refractometer (RI)

Examples of the maleimide compound used in the present invention include compounds represented by the following general formula (1).

在上述通式(1)中，n為1~50的整數，較佳為5~40的整數，進一步較佳為10~40。R¹ 獨立地表示選自碳原子數1~40、較佳為碳原子數6~40的直鏈或支鏈的亞烴基、任選具有雜原子的碳原子數3~40、較佳為6~40的二價環狀烴基、-O-、-NH-、-S-以及-SO₂ -中的1種或2種以上二價基團。

In the above general formula (1), n is an integer of 1-50, preferably an integer of 5-40, and more preferably 10-40. R ¹ independently represents a linear or branched alkylene group selected from 1 to 40 carbon atoms, preferably 6 to 40 carbon atoms, and 3 to 40 carbon atoms optionally having heteroatoms, preferably 6 ~40 divalent cyclic hydrocarbon group, one or more divalent groups among -O-, -NH-, -S- and -SO ₂ -.

In consideration of compatibility with (A) component, (B) component, and other components such as (D) component described later, heat resistance, etc., the carbon of a linear or branched alkylene group can be appropriately selected. Atomic number. Specific examples of the hydrocarbylene group include methylene, ethylene, propylene, butylene, 2,2-dimethylpropylene, hexylene, octylene, decylene, and dodecylene. Group, tetradecylene, hexadecylene, octadecylene.

The cyclic hydrocarbon group may be a homocyclic hydrocarbon group, a heterocyclic hydrocarbon group, or an aliphatic hydrocarbon group or an aromatic hydrocarbon group. In addition, the cyclic hydrocarbon group may be a monocyclic hydrocarbon group having a ring number of 1, or a polycyclic hydrocarbon group having a plurality of rings, or a condensed polycyclic hydrocarbon group formed by condensation of a plurality of rings. In the monocyclic hydrocarbon group, the number of atoms constituting the ring is preferably 3-10, more preferably 4-8, and still more preferably 5-7. In the condensed polycyclic hydrocarbon group, the number of atoms constituting the ring is preferably 8-20, more preferably 10-14, and still more preferably 10-12.

These may be used alone i.e. cyclic hydrocarbon group, it may also be used with a single bond or bonded to other groups represented by R ^1. Furthermore, the ring structure of the cyclic hydrocarbon group may have substituents such as an alkyl group having 1 to 20 carbon atoms, a monovalent unsaturated hydrocarbon group having 2 to 20 carbon atoms, a hydroxyl group, and a carbonyl group.

As said aromatic hydrocarbon group, the compound represented by the following general formula (10) and general formula (11) is mentioned, for example.

In the above general formula (10), R ⁷ represents a group selected from a single bond, -CH ₂ -, -O-, -S-, -SO ₂ -and -C(CH ₃ ) ₂ . R ⁸ each independently represents a group selected from a hydroxyl group and a linear or branched alkyl group having 1 to 6 carbon atoms. Among them, methyl or ethyl is preferred. a is preferably 0-4, more preferably 0, 1 or 2.

In the above general formula (11), R ⁹ each independently represents a group selected from a hydroxyl group and a linear or branched alkyl group having 1 to 6 carbon atoms, and is preferably a methyl group or an ethyl group. b is preferably 0-4, more preferably 0, 1, or 2.

Moreover, as the above-mentioned heterocyclic hydrocarbon group, the group represented by the following general formula (12) and general formula (13) is mentioned, for example.

In the above average composition formula (13), R ¹⁰ , R ^11, and R ¹² each independently represent a single bond, a hydrocarbon group having 1 to 40 carbon atoms, -O-, -NH-, -S-,- SO ₂ -and groups in -C(CH ₃ ) ₂ -.

Ring A and Ring B each independently represent furan, pyrrole, imidazole, thiophene, pyrazole, oxazole, isoxazole, thiazole, pyridine, pyrazine, pyrimidine, pyridazine, triazine, benzofuran, isobenzo Furan, indole, isoindole, benzothiophene, benzophosphorene, benzimidazole, purine, indazole, benzoxazole, benzisoxazole, benzothiazole, naphthalene, quinoline , Isoquinoline, quinoxaline, quinazoline, cinnoline and other ring-containing divalent groups. They may each have a substituent.

在通式(2)中，A獨立地表示含有芳香族環或脂肪族環的四價有機基團。B為具有任選含有二價雜原子的脂肪族環的碳原子數6~18的伸烷基鏈。Q獨立地表示碳原子數6以上的直鏈伸烷基。R獨立地表示碳原子數6以上的直鏈或支鏈的烷基。n’表示1~10的整數。m表示0~10的整數。In addition, as an example of the (B) maleimide compound used in the present invention, a maleimide compound represented by the following general formula (2) can be cited.

In the general formula (2), A independently represents a tetravalent organic group containing an aromatic ring or an aliphatic ring. B is an alkylene chain having 6 to 18 carbon atoms having an aliphatic ring optionally containing a divalent heteroatom. Q independently represents a linear alkylene group having 6 or more carbon atoms. R independently represents a linear or branched alkyl group having 6 or more carbon atoms. n'represents an integer from 1 to 10. m represents an integer from 0 to 10.

(需要說明的是，上述結構式中的未鍵合有取代基的鍵為與在通式(2)中形成環狀醯亞胺結構的羰基碳鍵合的鍵。)A in the general formula (2) represents a tetravalent organic group containing an aromatic ring or an aliphatic ring, and particularly preferably any tetravalent organic group represented by the following structure.

(It should be noted that the bond to which the substituent is not bonded in the above structural formula is a bond to the carbonyl carbon forming the cyclic amide structure in the general formula (2).)

Q in the general formula (2) is a linear alkylene group. These carbon atoms are 6 or more, preferably 6 or more and 20 or less, and more preferably 7 or more and 15 or less.

R in the general formula (2) is an alkyl group, which may be a straight-chain alkyl group or a branched-chain alkyl group. These carbon atoms are 6 or more, preferably 6 or more and 12 or less.

(需要說明的是，上述結構式中的未與取代基鍵合的鍵為與通式(2)中形成環狀醯亞胺結構的氮原子鍵合的鍵。) 作為通式(2)中的B，特佳為具有下述結構式表示的脂肪族環的伸烷基。

B in the general formula (2) is an alkylene group having 6 to 18 carbon atoms having an aliphatic ring optionally containing a divalent heteroatom. The number of carbon atoms of the alkylene group is preferably 8 or more and 15 or less. The alkylene group is a diamine compound derived from a raw material when synthesizing the maleimine compound. Examples of alkylene groups having one aliphatic ring include 1,2-cyclohexanediyl, 1,3-cyclohexanediyl, 1,4-cyclohexanediyl, and the like. In addition, as an example of an alkylene group having two aliphatic rings, an alkylene group represented by the following structural formula can be cited.

(It should be noted that the bond not bonded to the substituent in the above structural formula is the bond to the nitrogen atom forming the cyclic amide structure in the general formula (2).) As in the general formula (2) B is particularly preferably an alkylene group having an aliphatic ring represented by the following structural formula.

In the general formula (2), n'is an integer of 1-10, preferably an integer of 2-7. In general formula (2), m is an integer of 0-10, preferably an integer of 0-7, more preferably an integer of 1-7.

In the composition of the present invention, the content of (B) maleimide compound is preferably 10 to 90 parts by mass, more preferably 40 to 100 parts by mass of the total of (A) component and (B) component. 80 parts by mass, more preferably 50 to 80 parts by mass. Furthermore, in the composition of the present invention, the content of (B) the maleimide compound is preferably 5 to 80% by mass, more preferably 10 to 75% by mass.

(C) curing catalyst The (C) curing catalyst used in the thermosetting resin composition of the present invention includes (C1) a curing agent for epoxy resin, (C2) a curing accelerator, and (C3) a polymerization initiator. (C1) Curing agent for epoxy resin As the curing agent of the epoxy resin, a known curing agent can be appropriately selected. It is not particularly limited as long as it contains a functional group reactive with an epoxy group (hereinafter referred to as an epoxy reactive group). Examples of curing agents for epoxy resins include phenol resins, acid anhydrides, and amines. Among them, in consideration of the balance between curability and stability of the film state, it is preferably a phenol resin or a silicone-modified phenol resin.

Examples of the phenol resin include novolac type, bisphenol type, tris(hydroxyphenyl)methane type, naphthalene type, cyclopentadiene type, phenol aralkyl type, and the like. Among them, in order not to show a phase separation structure with the epoxy resin containing the silicone-modified epoxy resin, it is preferably the following silicone-modified phenol resin.

In each of the above general formulas, X is independently a hydrogen atom, an unsubstituted or substituted monovalent hydrocarbon group having 1 to 6 carbon atoms, an alkoxy group, or an alkoxyalkyl group. R ³ is an unsubstituted or substituted monovalent hydrocarbon group having no aliphatic unsaturated group, and the number of carbon atoms is 1 to 10, and the number of carbon atoms is particularly preferably 1 to 8. Examples include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, hexyl, cyclohexyl, octyl, and decyl; phenyl, xylyl, toluene Aryl groups such as benzyl groups, phenethyl groups, and phenylpropyl groups; and chloromethyl, bromoethyl, and trifluoromethyl groups in which part or all of the hydrogen atoms of their hydrocarbon groups are replaced by halogen atoms such as chlorine, fluorine, and bromine. Halogen such as fluoropropyl group is substituted for monovalent hydrocarbon group. R ⁵ represents an unsubstituted or substituted divalent hydrocarbon group optionally having an oxygen atom, and k is an integer of 8 or more, preferably 18 to 78, and more preferably 28 to 68. P is 0 or more, preferably 1-50, more preferably an integer of 1-10. R ^{5 is} preferably an alkylene group optionally having an oxygen atom or a hydroxyl group, etc., and examples thereof include the following groups. -CH ₂ CH ₂ CH ₂ --CH ₂ CH ₂ CH ₂ -O- -O-CH ₂ -CH(OH)-CH ₂ -O-CH ₂ CH ₂ CH ₂ -, -O-CH ₂ -CH( OH)-CH ₂ -O-CH ₂ CH ₂ CH ₂ -O- -O-CH ₂ CH ₂ CH ₂ --O-CH ₂ CH ₂ CH ₂ -O- It should be noted that in the above R ⁵ Among the groups exemplified by the divalent hydrocarbon group, the bond at the left end is a bond to the benzene ring having the group X of the general formula (14) or the benzene ring having the hydroxyl group of the general formula (15). The bond at the right end is a bond to the silicon atom of Si(R ³ ) ₂ of the general formula (14) or Si(R ³ ) _{2 of the} general formula (15). In addition, R ^{6 is} independently a hydrogen atom, a methyl group, or a trifluoromethyl group. The silicone modified phenolic resin can be used alone or in combination of two or more.

Examples of the acid anhydride include phthalic anhydride, pyromellitic anhydride, maleic anhydride, and maleic anhydride copolymers. Examples of the amines include dicyandiamide, diaminodiphenylmethane, diaminodiphenylmethane, and the like. These acid anhydrides may be used alone or in combination of two or more.

In the present invention, the curing agent is preferably a liquid curing agent, and particularly preferably a liquid curing agent at 25°C to 200°C. Among them, a bisphenol-type phenol resin or a novolak-type phenol resin that is liquid at 25°C is preferred, and the aforementioned silicone-modified phenol resin is more preferred.

The compounding amount of the curing agent of (C1) epoxy resin is preferably such that the epoxy reactive group in the curing agent is 0.8 to 1.25 equivalents relative to 1 equivalent of the epoxy resin of the epoxy resin of the component (A) , More preferably, the amount is 0.9 to 1.1 equivalents. If the compounding equivalence ratio (molar ratio) is less than 0.8, unreacted epoxy groups may remain in the obtained cured product, which may cause a decrease in the glass transition temperature or decrease in adhesion to the substrate. If the compounding equivalent ratio (molar ratio) is greater than 1.25, the cured product may become hard and brittle, which may lead to cracks during reflow or temperature cycling.

(C2) Hardening accelerator Examples of curing accelerators include 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 4-methylimidazole, 4-ethylimidazole, 2-phenylimidazole, 2- Phenyl-4-methylimidazole, 2-phenyl-4-hydroxymethylimidazole, 1-cyanoethyl-2-methylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole , 2-Phenyl-4,5-dihydroxymethylimidazole, 2-undecylimidazole, 1-decyl-2-phenylimidazole, 1-cyanomethyl-2-undecylimidazole, 2,4-Diamino-6-[2'-methylimidazolyl-(1')]-ethyl-secondary-triazine isocyanuric acid adduct, 2-methylimidazole isocyanuric acid adduct Products, 2,3-dihydro-1H-pyrrolidone (1,2-a) benzimidazole and other imidazole compounds. These imidazole compounds may be used alone or in combination of two or more.

In the composition of the present invention, relative to the total of (A) component and (B) component, the content of (C2) curing accelerator is preferably 0.05 to 20% by mass, more preferably 0.1 to 10% by mass, and more preferably Preferably it is 0.5-10 mass %. In addition, when the curing agent of (C1) epoxy resin and (C2) curing accelerator are used together as (C) curing catalyst, with respect to the total of (A) component, (B) component and (C1) component, ( C2) The content of the curing accelerator is preferably 0.05 to 20% by mass, more preferably 0.1 to 10% by mass, and still more preferably 0.5 to 10% by mass.

(C3) Polymerization initiator As the polymerization initiator, a thermal radical polymerization initiator and a photopolymerization initiator can be used, and a thermal radical polymerization initiator is preferred. The thermal radical polymerization initiator is not particularly limited as long as it can be used as a general polymerization initiator. As the thermal radical polymerization initiator, the decomposition start temperature in the rapid heating test (the temperature at which the sample starts to decompose when 1 g of the sample is placed on a hot plate and heated at a rate of 4°C/min) is preferably 40 ~140°C. If the decomposition start temperature is lower than 40°C, the storage property of the thermosetting resin composition at room temperature is deteriorated; if the decomposition start temperature is higher than 140°C, the curing time becomes very long, which is not preferable.

Specific examples of thermal radical polymerization initiators satisfying these conditions include methyl ethyl ketone peroxide, methyl cyclohexanone peroxide, methyl acetone acetic acid peroxide, acetone peroxide, 1, 1-bis(tert-butylperoxy)3,3,5-trimethylcyclohexane, 1,1-bis(tert-hexylperoxy)cyclohexane, 1,1-bis(tert-hexylperoxy)3 ,3,5-Trimethylcyclohexane, 1,1-bis(tert-butylperoxy)cyclohexane, 2,2-bis(4,4-di-tert-butylperoxycyclohexyl)propane, 1 ,1-bis(tert-butylperoxy)cyclododecane, n-butyl 4,4-bis(tert-butylperoxy)valerate, 2,2-bis(tert-butylperoxy)butane, 1,1-bis(tert-butylperoxy)-2-methylcyclohexane, tert-butyl hydroperoxide, p-menthane hydroperoxide, 1,1,3,3-tetramethylbutylperoxide Hydrogen, tert-hexylhydroperoxide, dicumyl peroxide, 2,5-dimethyl-2,5-bis(tert-butylperoxy)hexane, α,α'-bis(tert-butylperoxy) ) Dicumyl, tert-butyl cumene peroxide, di-tert-butyl peroxide, 2,5-dimethyl-2,5-bis(tert-butyl peroxide)-3-hexyne, iso Butyryl peroxide, 3,5,5-trimethylhexyl peroxide, octyl peroxide, laurel peroxide, cinnamic acid peroxide, m-toluene peroxide, benzyl peroxide , Diisopropyl peroxydicarbonate, bis(4-tert-butylcyclohexyl) peroxydicarbonate, di-3-methoxybutyl peroxydicarbonate, di-2-ethyl peroxydicarbonate Hexyl ester, di-sec-butyl peroxydicarbonate, bis(3-methyl-3-methoxybutyl)peroxydicarbonate, bis(4-tert-butylcyclohexyl)peroxydicarbonate, α ,α'-Bis(neodecylperoxy)dicumyl, cumyl peroxyneodecanoate, 1,1,3,3-tetramethylbutyl peroxyneodecanoate, neodecanoate 1-cyclohexyl-1-methyl ethyl decanoate, tert-hexyl peroxide neodecanoate, tert-butyl peroxide neodecanoate, tert-hexyl peroxide pivalate, tert-butyl peroxide pivalate, 2,5-Dimethyl-2,5-bis(2-ethylhexanoic acid peroxy)hexane, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate, 1-cyclohexyl-1-methylethylperoxy-2-ethylhexanoate, tert-hexyl peroxide 2-ethylhexanoate, tert-butyl peroxide 2-ethylhexanoate, isobutyl peroxide Tert-butyl peroxymaleate, tert-butyl peroxylaurate, tert-butylperoxy-3,5,5-trimethylhexanoate, tert-butylperoxy isopropyl mono Carbonate, tert-butylperoxymonocarbonate-2-ethylhexyl ester, 2,5-dimethyl-2,5-bis(benzylperoxy)hexane, tert-butyl peroxyacetate, peroxide Tert-hexyl benzoate, tert-butylperoxy m-tolyl benzoate, tert-butyl peroxybenzoate, bis(tert-butylperoxy) isophthalate, allyl tert-butyl peroxy Oxygen monocarbonate, 3,3'4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, etc. These polymerization initiators may be used alone or in combination of two or more kinds.

Among these thermal radical polymerization initiators, dicumyl peroxide, tert-hexyl hydroperoxide, 2,5-dimethyl-2,5-bis(tert-butylperoxy)hexane, α,α'-bis(tert-butylperoxy) dicumyl, tert-butyl cumene peroxide, di-tert-butyl peroxide, etc.

The compounding amount at the time of adding the polymerization initiator is preferably 0.5 to 10 parts by mass, and more preferably 0.5 to 5 parts by mass relative to 100 parts by mass of maleimine (B). It should be noted that, considering that the resin composition of the present invention is usually used under the illumination of fluorescent lamps, etc., the viscosity increases due to photopolymerization during use. Therefore, it is preferable that the resin composition does not substantially contain photopolymerization. Starter. Here, the "substantially not contained" means that a small amount of the photopolymerization initiator is contained to such an extent that the increase in viscosity is not observed, or the photopolymerization initiator is not contained at all. That is, in the present invention, it is preferable not to use a photopolymerization initiator.

(D) Other additives The resin composition of the present invention is obtained by blending predetermined amounts of the above-mentioned (A) component, (B) component, and (C) component. However, if necessary, it may be used within a range that does not impair the purpose and effect of the present invention. Other additives (D) components are added to the composition of the present invention. Examples of the additives involved include thermoplastic resins, inorganic fillers, organic solvents, flame retardants, ion trapping agents, antioxidants, tackifiers, low stress agents, colorants, coupling agents, and the like.

Examples of thermoplastic resins include polytetrafluoroethylene (PTFE) capable of imparting low dielectric properties to the resin composition of the present invention, especially the resin composition molded into a film, and PTFE whose surface is treated with silicon dioxide. , Modified polyphenylene ether (PPE), etc.

The purpose of adding the inorganic filler is to reduce the thermal expansion coefficient of the resin composition of the present invention and to improve the moisture resistance reliability of the resin composition. As the inorganic filler, for example, silicon dioxide (fused silicon dioxide, crystalline silicon dioxide, white silica, etc.), aluminum oxide, silicon nitride, aluminum nitride, boron nitride, titanium oxide, glass Fiber and magnesium oxide, etc. The average particle size and shape of these inorganic fillers can be selected according to the application of the composition of the present invention. Among them, spherical alumina, spherical fused silica, glass fiber, etc. are preferred. The blending amount of the inorganic filler is preferably 20 to 1500 parts by mass, and more preferably 100 to 850 parts by mass relative to the total of 100 parts by mass of the (A) component, (B) component, and (C) component.

The resin composition of the present invention may not contain a solvent, but it may be dissolved or dispersed in an organic solvent and used as a solution or dispersion (hereinafter simply referred to as "solution"). Examples of organic solvents include N,N-dimethylacetamide, methyl ethyl ketone, N,N-dimethylformamide, cyclohexanone, cyclopentanone, N-methyl-2-pyrrolidone, toluene, methanol , Ethanol, isopropanol, acetone, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, etc. Particularly preferred (B) the maleimide compound has an organic solvent solubility of 10% by mass or more at 25°C. As the particularly preferred organic solvent, methyl ethyl ketone, cyclopentanone, toluene, propylene glycol mono Methyl ether, propylene glycol monomethyl ether acetate. These organic solvents may be used individually by 1 type, and may use 2 or more types together.

The purpose of the addition of the flame retardant is to impart flame retardancy to the composition of the present invention. The flame retardant is not particularly limited, and all known flame retardants can be used. Examples of the flame retardant include phosphazene compounds, silicone compounds, zinc molybdate supported talc, zinc molybdate supported zinc oxide, aluminum hydroxide, magnesium hydroxide, molybdenum oxide, and the like.

The purpose of the addition of the ion trapping agent is to trap the ionic impurities contained in the resin composition of the present invention, and to prevent thermal degradation and moisture absorption degradation. It is not particularly limited, and all known ion trapping agents can be used. Examples of ion trapping agents include hydrotalcites, bismuth hydroxide compounds, and rare earth oxides.

All well-known antioxidants, tackifiers, low-stress agents, colorants, and coupling agents can be used, and they are not particularly limited.

The compounding amount of the component (D) varies according to the purpose of use of the thermosetting resin composition of the present invention. The component (D) other than the inorganic filler is preferably 5% by mass or less of the entire thermosetting resin composition of the present invention The amount.

＜Preparation method of composition＞ The thermosetting resin composition of the present invention can be prepared, for example, by the method described below. According to need, by simultaneously or separately heat treating (A) silicone modified epoxy resin, (B) maleimide compound and (C) curing catalyst, mixing, stirring, dissolving and/ Or disperse to obtain a mixture of (A) component, (B) component, and (C) component. In addition, at least one of inorganic fillers, mold release agents, flame retardants, and ion trapping agents, that is, other additives as the (D) component may be added and mixed with the above-mentioned (A) component, (B) component, (C) In the mixture of ingredients. Each component of (A) to (D) may be used individually by 1 type, and may use 2 or more types together.

The preparation method of the mixture and the device for mixing, stirring, and dispersing are not particularly limited. Specifically, for example, a crusher, a two-roll mill, a three-roll mill, a ball mill, a planetary mixer, a grinder, etc. having a stirring and heating device can be used. These devices can also be used in appropriate combination.

As a preparation method of the thermosetting resin film of the present invention, the (A) component to (C) component and (D) other additive components can be mixed in a predetermined composition ratio, and after the mixture is formed into a varnish , Using a coater or the like to coat the mixture on a suitable substrate and remove the solvent. As the substrate, for example, a polyester film coated with a silicone resin or a fluorine-containing resin having excellent mold release properties, or a polyester film that has been subjected to mold release treatment such as embossing, or the like can be used. The solvent can be removed by using, for example, a hot plate, hot air heater, infrared heater, etc., and heating at a given temperature/time. Here, the base material may be removed as needed, and a film or tape composed of only the packaging material may be directly formed. In the process of processing the composition of the present invention into a film, if the heating is not sufficient when removing the solvent, the solvent may remain in the film, resulting in voids, which may cause peeling/cracking. On the contrary, if the heating is excessive, the reaction between the epoxy resin and the curing agent may proceed, and the flexibility or adhesion of the film may be impaired. In addition, if the solvent is rapidly heated to a boiling point or higher, problems such as remaining voids in the film, on the surface of the film, or uneven thickness of the film may occur. Therefore, in the process of removing the solvent, it is preferable to adopt a method of gradually increasing the temperature below the boiling point of the solvent to remove the solvent. As a packaging method using a film, a semiconductor element can be packaged by compression molding or laminate molding. For example, using a compression molding machine, the molding temperature is 110-190°C, the molding time is 30-900 seconds, and the preferred molding temperature is 120-160°C and the molding time is 120-600 seconds. Furthermore, in any molding method, post-curing can be performed at 140-185°C for 0.5-20 hours. Example

Hereinafter, examples and comparative examples are shown to specifically explain the present invention, but the present invention is not limited to the following examples.

[Preparation of resin composition dispersion] The following ingredients were blended with the composition shown in Table 1, and a toluene solvent was added so that the solid content concentration was 60% by mass, and the mixture was stirred, mixed, dissolved, and dispersed using a ball mill to prepare a resin The dispersion of the composition (Examples 1 to 9, Comparative Examples 1 to 8). It should be noted that in Table 1, the amount represents parts by mass.

[Production of resin film] Using a slit coater as a film coater, the resin composition shown in Table 1 (Examples 1 to 9 and Comparative Examples 1 to 8) was applied to the release film (1): E7304 (manufactured by Toyobo Co., Ltd.) Polyester, thickness 75μm, peel force 200mN/50mm). Subsequently, by drying in an oven set at 100° C. for 10 minutes, a double-layer film in which a resin composition having a film thickness of 100 μm is laminated on the release film (1) was further produced. The release film (1) was peeled off from the double-layer film to prepare a film-like resin composition (resin film).

[Curing conditions of test piece] Unless otherwise specified, in the following evaluation methods, the curing conditions of the resin composition are set to be performed at 150°C for 4 hours.

(A) Silicone-modified epoxy resin (1) Epoxy resin (A): Silicone-modified epoxy resin (synthesized by the following method) (epoxy equivalent: 240) by the following general formula (16 ) Shows the partial allylated novolak type epoxy resin and the following general formula (17) represented by the hydrosilylation reaction of a linear organopolysiloxane containing hydrosilyl groups at both ends to synthesize a modified silicone性 epoxy resin.

(A') Epoxy resins other than silicone modified epoxy resins (1) Epoxy resin (A'): Bisphenol A type epoxy resin (trade name: jER828: manufactured by Mitsubishi Chemical Corporation) (epoxy equivalent: 189)

(在通式中，n表示1~10的數。) (2)雙馬來醯亞胺化合物(B2):(重均分子量30000、商品名：BMI-3000：DMI公司製造)

(在通式中，n表示1~10的數。) (3)雙馬來醯亞胺化合物(B3):(重均分子量700、商品名：BMI-689：DMI公司製造)

(4)馬來醯亞胺化合物(B4):(重均分子量15000、商品名：BMI-2560：DMI公司製造)

(在通式中，n表示1~10的數，m表示1~10的數。) (5)馬來醯亞胺化合物(B5):4,4'-二苯甲烷雙馬來醯亞胺(重均分子量351，在25⁰ C下對甲苯的溶解度＜1g/100g、商品名：BMI-1000：大和化成工業公司製造)(B) Maleimide compound (1) Bismaleimide compound (B1): (weight average molecular weight 16000, trade name: BMI-3000: manufactured by DMI)

(In the general formula, n represents the number from 1 to 10.) (2) Bismaleimide compound (B2): (weight average molecular weight 30000, trade name: BMI-3000: manufactured by DMI)

(In the general formula, n represents the number from 1 to 10.) (3) Bismaleimide compound (B3): (weight average molecular weight 700, trade name: BMI-689: manufactured by DMI)

(4) Maleimide compound (B4): (weight average molecular weight 15000, trade name: BMI-2560: manufactured by DMI)

(In the general formula, n represents the number from 1 to 10, and m represents the number from 1 to 10.) (5) Maleimide compound (B5): 4,4'-diphenylmethane bismaleimide (weight average molecular weight of 351, at 25 ⁰ C the solubility toluene <1g / 100g, trade name: BMI-1000: manufactured by Daiwa Chemical industries)

(C) curing catalyst (1) Imidazole curing accelerator (C1): 2-phenyl-4,5-dimethylolimidazole (manufactured by Shikoku Chemical Co., Ltd., trade name: 2PHZ)

(D) Other additives (1) Molten spherical silica: (average particle size 0.5μm, trade name: SO-25R: manufactured by Admatechs) (2) Phenoxy resin: Bisphenol A type phenoxy resin (weight average molecular weight 48,000, trade name: 1256B40: manufactured by Mitsubishi Chemical Corporation)

(1)Operability When the obtained film-like resin composition in a semi-cured (B-stage) state is bent at 180 degrees, no cracks or breakage will occur at all, and the case where it can be easily restored to its original shape is indicated as "○", and the film will be peeled off. The case where the film cannot be formed on the upper surface is indicated as "×".

(2) The adhesive force is such that the area to be bonded becomes 4 mm ² , and any film-like resin composition in Examples 1 to 9 and Comparative Examples 1 to 8 is placed on a silicon wafer with a size of 10 mm × 10 mm and placed on it After placing the silicon wafer, the film-like resin composition was cured under the above-mentioned curing conditions to prepare a test piece for testing the adhesiveness of the silicon wafer. Using this test piece, the shear adhesive force at 150° C. was measured with an adhesive tester DAGE-SERIES-4000PXY (manufactured by DAGE Corporation) as an evaluation of the adhesive force. It should be noted that the bonding area between the frame of the test piece and the film-like resin composition was 4 mm ² .

(3) Dielectric loss tangent A network analyzer (E5063-2D5 manufactured by Keysight Technologies, Inc.) was connected to a dielectric strip line (manufactured by KEYCOM Co., Ltd.), and the test piece in which the film-like resin composition was cured under the above-mentioned curing conditions was measured The dielectric loss tangent tanδ at a frequency of 1.0 GHz. The results are shown in Table 1 below.

(4) Determination of relative permittivity A network analyzer (E5063-2D5 manufactured by Keysight Technologies, Inc.) was connected to a strip line (manufactured by KEYCOM Co., Ltd.), and a test piece obtained by curing the film-like resin composition under the above curing conditions was measured The relative dielectric constant at a frequency of 1.0 GHz. The results are shown in Table 1 below.

(5) Wafer warpage Prepare a silicon wafer with a thickness of 775 μm and a diameter of 12 inches (300 mm). Using a vacuum laminator (manufactured by Takatori Co., Ltd, product name: TEAM-300M), and setting the internal vacuum degree of the vacuum chamber to 250 Pa, the film-like resin composition was attached to the above silicon at 120°C. On the chip. After returning the inside of the vacuum chamber to normal pressure, the silicon wafer was cooled to 25°C, taken out of the vacuum laminator, and the obtained wafer with resin film was placed in an inert gas oven at 150°C. The resin is cured by heating for 1 hour. The amount of wafer warpage after curing of the resin film was measured with a laser (manufactured by Toago Technology Co., Ltd, FLX-3300-T), and the obtained value is shown in Table 1. In addition, when the amount of warpage is too large to measure with this device, Table 1 shows the value measured using a ruler (JIS 1 level).

(6) Reliability A dicing machine (DAD685, manufactured by DISCO Corporation, spindle speed 40,000 rpm, cutting speed 20 mm/sec) with a dicing blade was used to obtain 10 mm× from the cured resin film-attached wafer obtained in the wafer warpage test 10mm square test piece. The obtained test pieces (10 pieces each) were subjected to a heat loop test (1000 cycles were repeated for a test that was kept at -25°C for 10 minutes and at 125°C for 10 minutes), and the heat loop was confirmed The state where the resin film after the loop test is peeled from the wafer. The test piece that did not peel off at all among the 10 test pieces was judged to be good, and even one of the 10 test pieces peeled off was judged to be bad, and the judgment results are shown in Table 1. In addition, since Comparative Examples 1, 3, and 4 could not be molded, and Comparative Example 5 was poorly cured, each test piece was not obtained. Therefore, the heat loop test could not be performed. In addition, since the test piece of Comparative Example 6 warped a lot and could not be cut, the hot loop test could not be implemented.

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Claims (10)

A thermosetting resin composition comprising the following components (A) to (C), (A) Silicone modified epoxy resin: 90-10 parts by mass; (B) Maleimide compound with a weight average molecular weight (Mw) of 2500 to 50000: 10 to 90 parts by mass; and (C) curing catalyst, However, the total of (A) component and (B) component is 100 mass parts. The thermosetting resin composition described in item 1 of the scope of the patent application further comprises (A') an epoxy resin other than (A) the silicone-modified epoxy resin. The thermosetting resin composition described in item 1 of the scope of patent application, wherein (A) silicone modified epoxy resin is at least one silicone modified ring represented by the following general formula (8) or general formula (9) Oxygen resin,

In the general formula (8) and general formula (9), X independently represents a hydrogen atom, an unsubstituted or substituted monovalent hydrocarbon group with 1 to 6 carbon atoms, an alkoxy group or an alkoxyalkyl group, R ³ Represents an unsubstituted or substituted monovalent hydrocarbon group without an aliphatic unsaturated group, R ⁴ represents a glycidyl group, R ⁵ represents an unsubstituted or substituted divalent hydrocarbon group optionally having an oxygen atom, and R ⁶ represents independently of each other A hydrogen atom, a methyl group, or a trifluoromethyl group, k is an integer of 8 or more, and p is an integer of 0 or more. The thermosetting resin composition according to the first item of the patent application, wherein (B) the maleimide compound is a bismaleimide compound represented by the following general formula (1),

In the general formula (1), n is an integer from 1 to 50, and R ¹ independently represents a linear or branched alkylene group selected from 1 to 40 carbon atoms, and the number of carbon atoms optionally having heteroatoms is 3. ~20 divalent cyclic hydrocarbon group, one or two or more divalent groups among -O-, -NH-, -S- and -SO ₂ -. The thermosetting resin composition as described in claim 1, wherein (B) the maleimide compound is a compound represented by the following general formula (2),

In the general formula (2), A independently represents a tetravalent organic group containing an aromatic ring or an aliphatic ring, and B is an alkylene chain having 6 to 18 carbon atoms with a divalent aliphatic ring. The divalent aliphatic ring optionally contains heteroatoms, Q independently represents a straight chain alkylene group with 6 or more carbon atoms, R independently represents a straight or branched chain alkyl group with 6 or more carbon atoms, and n'represents 1 An integer of ~10, and m represents an integer of 0-10. The thermosetting resin composition according to the fifth item of the scope of patent application, wherein A in the general formula (2) is represented by any one of the following structures,

However, the bond to which the substituent is not bonded in the above structural formula is a bond to the carbonyl carbon forming the cyclic amide structure in the general formula (2). The thermosetting resin composition according to item 1 of the scope of patent application, wherein the (C) curing catalyst is selected from the group consisting of (C1) epoxy resin curing agent, (C2) curing accelerator and (C3) polymerization start At least one of the agents. The thermosetting resin composition according to the first item of the scope of patent application, wherein the curing catalyst (C) is an imidazole compound. A thermosetting resin film comprising the thermosetting resin composition described in item 1 of the scope of patent application. A semiconductor device is packaged with a thermosetting resin film as described in item 9 of the scope of patent application.